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Guaiacol → Methyl 4-(2-methoxy-phenoxy)-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate

HRID 1738626
ノート
印刷プレビュー

反応式

HRID 1738626 の反応式
Cl[C:2]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23].C(=O)([O-])[O-].[K+].[K+].[C:31]1([O:38][CH3:39])[C:32](=[CH:34][CH:35]=[CH:36][CH:37]=1)[OH:33]>CC(C)=O>[CH3:39][O:38][C:31]1[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=1[O:33][C:2]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 23288648Methyl 4-chloro-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate

生成物 1

HCID 23288681Methyl 4-(2-methoxy-phenoxy)-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

4.28 g of methyl 4-chloro-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate were dissolved in acetone (250 ml), treated at RT with 5.0 g of potassium carbonate, 1.93 of guaiacol and the mixture was heated at reflux for 20 hours. It was poured on to ice-water and extracted with ethyl acetate. The organic phase was washed 3 times with 5% sodium hydroxide solution, then with water, dried over sodium sulphate and finally concentrated on a rotary evaporator. The crude product (6 g) was flash chromatographed on silica gel with hexane/ether (1/1). here was thus obtained the desired methyl 4-(2-methoxy-phenoxy)-3-nitro-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoate as a pale yellow powder.

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 20 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed 3 times with 5% sodium hydroxide solution
  5. dry with materialwith water, dried over sodium sulphate
  6. concentrationfinally concentrated on a rotary evaporator
  7. customchromatographed on silica gel with hexane/ether (1/1)

出典と根拠

ORDレコード
ord-64d4d74695bd44529cab07dff92ab0b1
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05962682

反応ノート

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